


A Match made in Heaven

by suckerfordeansfreckles



Category: Supernatural
Genre: Awkward Flirting, Blushing Dean, Boys Kissing, Castiel and Claire are siblings, Castiel/Dean Winchester First Date, Castiel/Dean Winchester First Kiss, Claire Novak Ships Castiel/Dean Winchester, Claire is 12 years old, Dean In Love, Dean Winchester Has a Crush on Castiel, Dean helps Sam befriend Claire, Dean wooing Castiel, DeanCas - Freeform, Destiel - Freeform, Falling In Love, First Dates, First Kiss, Frottage, M/M, Making Out, Other Additional Tags to Be Added, Pining, Presents, Sam Ships It, Sam Winchester Ships Castiel/Dean Winchester, Sam admires Claire, Sam and Claire are best friends, Sam and Claire help Dean win over Castiel, Sam is 11 years old, Sam wants to be Claires friend, Slow Burn, Smut, Wooing
Language: English
Status: Completed
Published: 2017-09-03
Updated: 2018-05-05
Packaged: 2018-12-23 10:17:43
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 13,346
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11987772
Author URL: https://archiveofourown.org/users/suckerfordeansfreckles/pseuds/suckerfordeansfreckles
Summary: Dean's little brother Sammy has been talking about Claire Novak, who's a class above him, for about two weeks non-stop. 11-year-old Sam admires Claire and desperately wants to be her friend, so he and Dean start planning how to make a friendship happen between them.When Sam and Claire actually become friends, Dean coincidentally meets Claire's big brother Castiel and falls head over heels for the gorgeous, blue-eyed boy. From that moment on, Sam and Claire are the ones helping Dean to woo Cas. The whole process naturally involves lots of pining, awkward flirting and a constantly blushing Dean.





	1. Chapter 1

**Author's Note:**

> Hey there! :)
> 
> This is my first ever fic with multiple chapters and I'm super nervous about posting it.  
> I REALLY hope you guys like it enough to keep reading!!

Dean has just placed the hot bowl of spaghetti on the table when he hears his little brother closing the front-door. He and his 11-year-old brother Sammy have been living together in their own little apartment for a year. When their parents died in a car accident five years ago, they lived with their uncle Bobby until Dean’s eighteenth birthday last year. With his birthday, he finally became Sam’s legal guardian. He has worked hard to reach that point, quit school with 16 and started working as a mechanic to save money to provide a home for himself and his little brother and saved money for Sammy’s education ever since.

 

The last year has worked out pretty great for them and Dean is proud of how he’s able to balance being a big brother, a mom and a dad to Sam, all at the same time. He’s working at a garage from morning till late afternoon, but still manages to take care of Sam in the mornings to, pack him a snack for school, get home to cook dinner for them and spend the rest of his afternoon and evenings with Sammy. Because of his working hours, Sammy has to spend some hours at their uncle’s house every day, but both he and Bobby enjoy their time together, so Dean doesn’t feel that bad about leaving Sam with Bobby. 

 

About two months ago he started picking up night-shifts at a bar two streets away, because it’s easy to run short on money with a kid that grows two inches every month and needs new clothes regularly. The fact that Dean would be able to sprint back home from the bar anytime Sammy needs him and it wouldn’t take longer than 6 minutes- not that he tested this theory…- doesn’t make him feel less awful about leaving his baby brother alone at night. The thing is, he really wants to be able to provide Sam everything he needs and wants, so he eventually has to stop worrying so much about him. Sam is old enough to be on his own sometimes, anyways.

 

Dean places two plates and cutlery on the table when Sam enters their little kitchen, a big, gummy smile plastered on his face. It’s the fifth time over the course of the last two weeks that Sammy has come home with a dreamy look and a secret smile on his face. He acts way sneakier than he has to, considering that Dean definitely knows what, or rather who, has him smiling like that. To be honest, he has already heard so many different stories about that “fierce, super cool” girl a grade above Sam and her “kind smile and courage”, that he’s a tiny bit annoyed about his brother’s admiration for her. He suspects that Sam has a tiny crush on this Claire, but every time he brings it up, Sam denies just that. Sammy says that he simply wants to befriend her because she seems like an amazing person and would surely be cool to spend time with.

 

To be honest, Dean is less annoyed about Sammy admiring her than about the fact that the boy doesn’t just go talk to Claire. If she’s as nice as Sammy makes him believe she is, there shouldn’t be any problem with that at all.

 

“Dean, can I tell you what happened today?” Sam asks, sighing happily as he plops down on a chair.

 

“You know I love to hear about your day, buddy! Was it Claire?” Dean winks at his blushing brother, handing him a bowl. “Grab some spaghetti before they get cold, though. I made your favorite vegetable sauce, by the way.”

 

“Aw yes! Thanks, De.”

 

The kitchen is filled with clattering until Sam’s bowl is filled up to the brim with noodles and he starts talking again.

 

“So, get this. Claire smiled at me today! She dropped one of her books on the way to her classroom and I picked it up to hand it back to her- and she thanked me and smiled!! And I’m sure it was directed at me, this time,” Sam beams while he rolls up some spaghetti with his fork.

 

“Awesome, Sammy! Did you talk to her?” Damn, Sammy’s excitement is just too cute for Dean to keep being annoyed.

 

“Well, not really. You know I don’t know how to start a conversation with her. She’s just so cool and she’s a year older than me, Dean! She’ll probably laugh at me…,” Sam mumbles, eyes fixed on his bowl of food.

 

“Come on, you told me she’s super nice and friendly! I’m sure she won’t laugh at you if you’d just try to approach her. She should be honored by you trying to be her friend,” Dean says with a serious face. “You need some help with that? You know I’d do everything for you.”

 

“Would you really help me? That would be so cool!” And there’s the excited puppy expression (Dean secretly loves) back on his face once again. “I mean, you have loads of experience with people. Maybe with your help we could be friends!”

 

That earns him a fond smile of his big brother. “Sure thing, Sammy! We can plan how we’re gonna win her over after dinner.”

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

On the next morning, Sam leaves home with not only one, but two slices of Dean’s homemade apple pie. The first step in their plan to approach Claire was for Sammy to offer her some of his food at lunch time. Dean hopes that she’ll accept it and they finally start talking over some food. Last night, they made a list about everything Sam knows Claire likes and decided to just go from there and hope for the best. Some small presents, nice gestures and food should probably be enough. Sammy is nice, funny and considerate Dean doesn’t doubt that Claire is going to like him a lot, as soon as she gets to know him.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

If the big smile Sammy shows as soon as he enters their apartment on that evening means anything, step one seems to have worked quite well. 

 

“We actually talked, De! It worked, you’re a genius,” Sam shouts and Dean has his arms full of his gangly, nerdy, little brother even before the latter bothered to get rid of his shoes or his raincoat.

 

Before he can let go of him, his puppy of a brother starts bombarding him with questions. “Okay, so what’s next? What are we gonna do tomorrow? Do you think we could actually become friends, though??”

 

Goddammit, Dean loves his overexcited little brother so much.

 

“How about we bake her some cookies?”

**Notes for the Chapter:**

> Find me on [Tumblr](https://suckerfordeansfreckles.tumblr.com)  
> I'd love to talk to you :)


	2. Chapter 2

They spend the rest of their evening making a mess of their kitchen, leaving flour and smudges of cookie batter not only all over the room but also all over each other, thanks to some impromptu batter-fights. They end up dirty and giggling, but with two trays of delicious, soft chocolate chip cookies. Since Sam hadn’t stopped begging for it, they used his favorite food coloring on some of them, so five of their once oh so beautiful cookies now are of a venomous looking blue. Sam already ate half of a blue cookie, ignored all of Dean’s protests and made him eat the other half, and is currently putting the rest of them into one of Dean’s tupperboxes for school tomorrow.

 

“So, you think she’ll like them, Sammy?” Dean turns his head towards his brother, who is putting the cookie-box into his school bag, while wiping the cookie batter off the kitchen counter with a wet rag.

 

“I know she’ll love them! Especially the blue ones,” Sam answers with a cheeky grin. 

 

“Nonsense, I bet she’s gonna think you’re trying to poison her!” Dean laughs, picks up one of the batter-smeared spoons and wipes it off on Sammy’s cheek.

 

“Hey! That’s unfair, I have no weapon to defend myself,” Sam giggles and pretty much tackles his big brother in a hug and rubs his face on Dean, to clean his cheek on the front of Dean’s already ruined shirt. Dean returns the hug with a chuckle and gently pats Sam’s shoulder. “She likes blue, she wears blue stuff all the time! Also, who wouldn’t want to eat blue cookies? Everyone thinks they are super cool – except for you, old man.” With that, a giggling Sam unwraps himself from Dean’s arms and starts sprinting out of the room.

 

“Old man? I’ll show you what this old man can still do to you,” Dean shouts, throwing the rag in the general direction of the sink and chasing after his squealing brother through their apartment.

 

Once he catches him, Dean heaves Sammy up into the air, gently throws the heavy sasquatch down on their old leather couch and finally starts tickling him mercilessly. It takes some time, because Sam is quite stubborn and hates to give in, but he eventually forces a giggled apology out of his little brother. After a quick glance on the clock, Dean sends him off to take a shower and get ready for bed, though. 

 

Dean gets back to cleaning the kitchen until it’s time to switch off the lights in Sam’s room and wish him a good night. 

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

When Sam gets home the following day, he’s all smiles. He definitely exaggerates a bit when he tells Dean how it went with Claire; the girl in his story loved the cookies so much that she practically inhaled the first three of them in five seconds flat, thanked Sammy for them about seven times and asked for the recipe almost twice as often.

 

How it actually went down doesn’t matter, to Dean it’s just important that the cookies were a success. And, considering that Sam pretty much beams like the sun for the rest of the day, they definitely were. He and Claire apparently had a long talk and soon found common interests like their love for Star Wars, detective novels and basketball. Their interest in basketball lead to Claire inviting Sam to watch one of her team’s games on Saturday. Sammy is over the moon, especially since she told him that her team has been searching for a new member for quite some time, and that he should consider joining them.

 

Sammy couldn’t shut up about how cool it would be to join the team and spend more time with Claire for the rest of the day- he goes on and on about how confident and helpful Claire was today and how nice she treats him. 

 

So, because he’s an amazing big brother, Dean calls Bobby as soon as Sam’s tucked in for the night to rescheduled their lunch-date with him from Saturday to Sunday. This way, the brothers would be able to watch Claire’s game in two days. 

 

As much as Dean would like to pretend that he’s doing it out of selfless love for his brother, if he’s being honest, he probably wouldn’t be able to take more than those two days of Sammy constantly talking about Claire and the basketball team. He really isn’t that keen on spending his Saturday afternoon watching sweaty kids play basketball, but this way he at least finally gets to know Claire. And Sammy’s gonna be happy, so he’ll survive it.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

Saturday comes around pretty fast and Dean finds himself in the parking lot of a small school in a tiny village with a fidgety, hyperactive Sam in the passenger seat, way too soon for his liking. 

 

According to Bobby, who had to deal with Sammy until Dean got home from work, his baby brother had been impatiently running around their apartment the whole day. Apparently, Sam had been distributing wastepaper bins all over their flat to practice his basketball skills by crumpling up paper and trying to throw the paper balls into the bins. The second Dean had entered the house, he’d been bombarded with questions about when they were finally going to leave and see Claire.

 

Sam practically jumps out of the Impala as soon as Dean parks the car and shuts off the engine, who in turn has to scramble after his little brother and grab his shoulder to slow him down. Yes, they are in a small village, there probably won’t be a lot of traffic and Sam should be old enough to keep an eye out for any driving cars but they are in a parking lot and Sammy is distracted right now- Dean won’t risk anything by letting him run off on his own.

 

He keeps him by his side until they enter the gym, but lets go of him as soon as a blond girl in a green jersey spots Sam and starts waving him over. With a “That’s Claire, I’m gonna go say hi!” thrown over his shoulder, Sammy takes off and leaves Dean on his own.

 

The benches that are framing the wall of the small, like sweat and rubber smelling gym, are quite full already, so Dean takes a seat right between a dad with a beer-belly and a knitting (what the hell?) grandma and watches Sammy interact with Claire. They seem to get along with each other really well and it doesn’t take long until Claire is pulling Sam from player to player by the sleeve of his shirt, apparently introducing him to her team. She’s halfway through her team when their coach, a tall, elder man with dark hair and a grim expression, blows his whistle and the kids gather on the court to start the game. Sam shouts something that sounds like “good luck” in Claire’s direction and comes running back towards Dean. 

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

Claire’s team, the Green Dragons, as an exasperated Sam had explained to Dean five times over the course of the game, lost. They don’t seem to mind that though, they all still grin and give each other high fives. As soon as the crowd starts thinning, Claire walks over to them and introduces herself to Dean- with a handshake and everything. Dean’s honestly pretty impressed by the small, petite blond girl and her polite way. 

 

She’s about a head smaller than Sam, but she balances it out quite well with her confident posture and cheerful attitude. Sammy’s been right after all, she seems like a really cool girl.

 

“Is it okay if I introduce Sam to my coach? I don’t know if he told you, but our team is in need of a player, and- if you’re okay with it- and Sam really wants to- I’m sure the coach would let him join immediately,” she says and brushes a strand of hair out of her face and behind her ear. 

 

“Of course! I’ll wait here. Go show off your skills, Sammy,” Dean grins and leans back against the wall. He watches the three of them talk and after Sam has happily shown off his throwing skills, Dean talks to the coach, Rufus Turner, about the organizational details like practice dates, money and so on.

 

Seems as if Dean’s going to spend quite some time in this smelly gym after all, probably starting with Sam’s first practice next Wednesday.

**Notes for the Chapter:**

> Guess who Dean will meet in the same smelly gym for the first time ;)
> 
> Big thank you to everyone who has the patience to read this, it won't take long until the big pining and wooing finally begins- I promise! <3
> 
> Talk to me on [Tumblr](https://suckerfordeansfreckles.tumblr.com) ?


	3. Chapter 3

**Notes for the Chapter:**

> Hey guys! 
> 
> I finally managed to get over my weird writing mood!  
> I'm so sorry it took me that long to update this fic but I'm going to try and actually update in reasonable time intervals from now on... 
> 
> In this chapter, Dean first (kind of ???) meets Cas. And embarrasses himself. And just genuinely loves and supports Sammy.

Since Dean usually has to work during the time Sammy has basketball practice on Thursdays, Bobby- bless him for being this supportive and invested in Sam’s life- has been accompanying him to his basketball practice for the last two weeks. And that’s the exact reason why Dean is obligated to join and watch Sammy’s first game this week-end.

 

They arrive at the gym way too early, because Sam has insisted on driving there at least 40 minutes earlier than they would have needed to, because “Dean, what if there’s a traffic jam, or your car breaks down, or you take a wrong turn somewhere- and I miss my first game?!”. Sam even stubbornly insisted on driving to the gym in his sports clothes this morning, because he wanted to be ready to get going as soon as he enters the sports hall. Which left Dean hurriedly packing a gym bag with fresh clothes for Sammy to put on after the game literally five minutes before they had to leave their apartment.

 

And now Dean is sitting in an empty gym, watching Sammy jump around and do what he calls his “warm-up”, desperately willing the time to move a little faster. There are still 20 minutes left until the team is supposed to meet at the sports hall, and about 40 minutes until the game actually starts. Also, it’s not even fucking seven a.m. on a goddamn Saturday! Nobody can judge Dean for falling asleep leaning against the wall this early in the morning, especially not since he returned home from a night-shift at the bar just a few hours ago.

 

That doesn’t mean he isn’t embarrassed as hell when he finally wakes up, though. Dean awakes confused and grumpy, thinks about just falling back asleep- until he realizes where he is. He shoots up and off the wall, quickly taking in what’s going on around him and trying to guess how long he’s been asleep for. He’s lucky and finds that the game hasn’t even started yet, though there already are a few people sitting on the benches around him and watching the kids preparing for the game. 

 

The guy next to Dean on the bench has apparently been startled by Dean’s aggressive way of waking up, because he’s currently blinking at Dean owlishly, fixing him with incredibly blue eyes and a slightly tilted head. 

 

Dean only has a few seconds to take in the tousled dark-brown hair, the unbelievably sharp jawline and the way this dude’s black shirt stretches deliciously over his broad shoulders and chest. Before he can even send him a smile, what seems like a whole freaking family takes a seat between the two boys, squeezing themselves in the 5 inches-wide space on the bench between them.

 

Dean tries to catch the blue-eyed guy’s gaze again, but just when he leans forward, hands braced on his knees, the coach blows his whistle to signal the start of the game. Dean ignores this weird, overpowering need to interact with the boy he suddenly feels, in favor of focusing his attention on the game. 

 

It doesn’t take him long to find his sasquatch brother in the crowd of hyped-up kids, and when he does, Sam meets Dean’s eyes with a grin too big to be healthy. He shoots his big brother a thumbs-up before putting on what’s probably supposed to be his ‘I am so incredibly concentrated’-face (but looks more like his ‘I am so incredibly constipated’-face, if you were to ask Dean) and focuses on the game himself. 

 

The game is actually pretty interesting and Dean soon finds himself really engrossed in what’s happening. The crowd is, unfortunately, not really responsive; all the kids get for scoring is quiet applause and a few nice words like “Good work!”, “You go, Sarah!” or “Nice throw!”.

 

Which is why, in hindsight, Dean’s reaction to Sammy’s first score is pretty damn embarrassing. The kids have been playing for about half an hour when Sammy gets ahold of the basketball, shoots it towards the hoop and actually scores!

 

Dean is up and cheering without a second thought, throwing his hands in the air and screaming from the top of his lungs, drowning the meager applause. “Damn YES!! Freaking awesome, Sam! That’s a real Winchester, right here- look at him killing the game!” 

 

For a few seconds, the gym grows even more quiet, and what feels like every single person in there is staring at him. From his position, he has a great few over the crowd, and for a moment he catches the dark-haired guy’s eyes. He notices him looking directly at him and grinning like crazy, and because Dean apparently doesn’t have his body under control anymore, he starts blushing furiously. 

 

And that marks the moment he finally realizes that he just embarrassed himself in front of his little brother’s new team and a huge part of their families and friends. 

 

Which means, Sammy is probably going to be ten times more embarrassed than Dean himself, and Dean is likely to never hear the end of this. He shoots a concerned look towards Sam- and finds him, thank fuck, beaming from ear to ear at his goofy big brother! He’s lucky Sam still cares so much about his opinion and support, otherwise he might have had to deal with Sammy’s newfound preteen-bitchyness for the next few days because he just behaved like that in front of his new friends.

 

Dean sends a thumbs-up and a proud grin towards his brother before plopping back down on the bench, ignoring the weird look he gets from the woman besides him and continues watching the game.

 

The time goes by way faster than Dean would have anticipated and in no time at all the coach ends the game and the Green Dragons are squealing and jumping around and celebrating their win, while their competitors sulk. Soon, all kids are retreating to the changing rooms and Dean is left waiting for his brother in a sports hall that’s suddenly buzzing with life, as parents are starting to strike up conversations with each other or attempt to squeeze out of the gym to get some fresh air. 

 

Dean gets up and starts desperately looking for blue eyes and dark hair in the crowd, hoping to actually get a chance to talk to the guy. Before he can find him, though, Sam is standing in front of him in his fresh clothes and suddenly tackles him in a hug. 

 

“That was so much fun! Thanks for letting me do this, De.” He giggles into his brother’s shoulder.

 

“Hey, I’m glad you enjoy playing basketball so much! Also, you kicked ass- you actually are freaking amazing at this. You being freakishly tall finally has its advantage,” Dean grins and ruffles his hair. “You better thank Bobby for driving you to practice all the time, though. Don’t take that for granted!”

 

“Sure, I‘m gonna do that when I see him in a few days!” Sam agrees eagerly.

 

“You better! Come on, let’s head home. I might even make celebratory burgers for dinner, if you hurry up.”

 

Sam’s up and at the door in a few seconds, pulling Dean with him and dragging his gym bag along with him with his other hand. The gym is pretty empty now, but Sammy still turns, waves at the last few kids and shouts his goodbye before they head towards the car.

 

The first half of their drive home is uncharacteristically quiet, up until Sam tentatively starts a conversation. “Listen, Dean. Claire actually asked if we could meet outside of school and basketball practice. What do you think?”

**Notes for the Chapter:**

> First of all, a huge thank you to everyone still bothering to read this! It means a lot to me <3
> 
> Find me on [Tumblr](https://suckerfordeansfreckles.tumblr.com)  
> I'd love to talk to you! :)


	4. Chapter 4

“So, where does Claire want to meet you?” Dean asks carefully, eyes still fixed on the street.

 

“She- um, she asked if I want to come over to her place…” Sam mumbles, apparently knowing exactly how Dean will react to this answer.

 

“Sammy, you know the rules,” Dean sighs and casts him a quick look. “You guys haven’t been friends for that long and I don’t know Claire’s family.”

 

“You could drive me there and meet them, though!!” Sam tries again. “I told Claire you usually don’t let me stay over at someone’s place until you know their family, and she said you could just come over with me and get to know her brothers.”

 

“She, um… she lives with her brothers?” Dean’s definitely curious now, and the mischievous grin he catches on Sammy’s face tells him that his tiny devil of a brother knew he’d get this reaction out of him.

 

“Yes! It’s not like it is with us, though, like you and I are a little family. Claire has a dad, but he writes books or something and spends a lot of time travelling- and her mom left them when she was a baby. She’s living with her two brothers and they take care of her.” Sam grins triumphantly. He knows exactly that Dean can’t say no to meeting Claire’s brothers under these circumstances, he knows Dean would love to talk to young people who are taking over the role of a parent for their sibling. 

 

“Well… when were you two thinking about meeting?” 

 

“YEEEEEES, DEAN THANKS!! You really are the best,” Sam starts squealing.

 

Awesome, now Dean has to deal with a bouncy, hyperactive puppy for the rest of the drive… He just hopes Sammy won’t act like that every day until this little get-together actually happens.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

 

“Dee, I need your help. Can I come in?”, Sammy’s voice comes through the door to Dean’s room. From the way it sounds, his face is squished up against his big brother’s door as he waits for Dean to let him in. 

 

“Sure thing, sasquatch. But beware that your beautiful brother is not yet wearing a shirt.” Dean shouts back as he starts browsing through his closet to find a nice-but-not-too-nice shirt for the occasion. “Just so you’re warned and not get a sudden heart-attack because I’m too gorgeous for you to handle.”

 

“I’m pretty sure you got something wrong there, grandpa,” Sam giggles as he barges in and flops down on the bed. He’s still in his pajama as he watches Dean put on a black shirt and his favorite blue flannel. “Ah, I knew you’d wear this one!”

 

“That a problem?” Dean asks gruffly as he checks his hair in the mirror. “You aren’t even ready yet and we’re supposed to be at Claire’s in, like, half an hour. What do you need my help with?”

 

“So, I just wanted to see if you’d actually wear this flannel. And… you know, since I have the same one, I wanted to ask…” Sammy trails off and looks at Dean with huge hazel puppy eyes. 

 

Dean grins and answers Sam’s unspoken question, already knowing what his little brother wants. “Yeah, sure you can wear the same one. Wouldn’t be the first time we’re looking like twins,” Dean laughs and before he can even send Sam a wink, his little brother is up and out of the room to get changed.

 

Dean goes to fetch his wallet and keys and once he reaches the door, he finds Sam already waiting for him in a black shirt, his very own blue flannel and blue jeans. To be honest, Dean loves little moments like that. Sammy is 11 years old and still wants to look like his big bro, and if that doesn’t show how much he still sees him as a role model, Dean doesn’t know what does. To be fair, he had worked very hard to be a person Sam could look up to one day, so he doesn’t feel like denying himself to be proud about things like that.

 

He can’t suppress a tiny, happy smile as they make their way to the car. To Dean’s surprise, it actually only takes them ten minutes to reach Claire’s street and park the Impala. Sammy practically pulls Dean out of his car and towards a small house, where Claire’s already standing in the front yard and waving at them frantically.

 

The closer they get to the girl, the bigger her smile seems to get- and as soon as Sammy is close enough for her to reach him, she pulls him into a hug. “It’s so cool you could make it! I’ve been really excited for today, there’s so much I want to show you around the house. I think I want to show you my room first, and then the tree house,” she breaks her rambling for a second to offer Dean her small hand in greeting. “And my brothers have been very curious about you, Dean. They can’t wait to meet you.”

 

Dean can’t help it, Claire’s bubbly mood is infectious and he finds himself following the kids towards the house with a big smile and a giddy feeling in his stomach. 

 

He honestly has been looking forward to today a lot. He never had the opportunity to talk to someone his age who is caregiver and psychological parent to their younger sibling. Yes, he spent hours on the internet chatting with people and looking for tips and pointers on how to handle a situation like that, but it’s nothing compared to being able to talk about your experiences face to face with someone who actually gets it. 

 

Even before they reach the door to the house, it slams open and they are greeted by a small guy with brown hair and a smirk on his face. He looks quite a lot older than Dean, maybe 28? “Ah, you must be Sam and Dean. Welcome to the Casa Novak. Come on in!” 

 

Dean’s only two steps into the house and already feels absolutely welcome. Upon entering, he finds himself in a rather large, bright hallway, filled with tons of shoes and coats. It’s one of the things Dean has always appreciated in other’s homes- a little derangement makes a place feel a lot more lived-in and homey.

 

Once the brothers are out of their boots and jackets, Claire immediately starts pulling Sam towards the staircase that leads up to the second floor. Sam shoots him a questioning look, but as soon as Dean nods his permission, the two bolt up the stairs with matching grins and he’s left with the tiny, mischievous looking guy.

 

“So, I’m pretty sure I forgot to introduce myself? I’m Gabriel Novak, the oldest one,” he grins and gives Dean a friendly pat on the shoulder. “My younger brother Castiel is in the kitchen, preparing some drinks and snacks. Follow me.” 

 

Dean follows the bossy little dude into the living-room. It’s an inviting, decent-sized room with a huge leather couch, an ancient looking armchair, a few wooden cabinets, and plants and flowers crammed on every windowsill and empty surface. 

 

Dean sits down on the couch and Gabriel takes a seat on the chair across from him. “Hey, first of all, thank you for inviting us over. Sammy’s been really fucking hyped up for this for days,” Dean says.

 

“Claire has been, too. She started writing several lists about what to do once Sam finally gets here,” Gabriel snorts and rolls his eyes. “It’s been really hard to get her to calm down, especially today.”

 

“Yeah, you can say that again!” A deep voice interjects. 

 

Dean’s head shoots up towards where the rich voice came from, and his eyes lock with incredibly blue ones. Blue eyes he has definitely seen before. 

 

And that’s when it hits him; the dark hair, the blue eyes, the stubble, the damn cheekbones. This is the exact same guy he has drooled over on Sammy’s first game a week ago. And he’s standing right in front of Dean, in sweatpants and a simple black shirt, hair in disarray and balancing a plate of cookies and pale-blue teacups on a tray. 

 

And he looks fucking gorgeous.

**Notes for the Chapter:**

> YES, THEY FINALLY OFFICIALLY MET!   
> I'd love to hear what you think about this chapter in the comments :)
> 
> Talk to me on [Tumblr](https://suckerfordeansfreckles.tumblr.com/)?


	5. Chapter 5

**Summary for the Chapter:**

> Basically, they just get to know each other and spend a chill morning/ afternoon with each other. Also, the pining begins.

**Notes for the Chapter:**

> I'm so sorry it took me so long to update again... I'm horrible :(

Dean can’t help but stare a little longer at the beautiful man in front of him, taking in his effortless beauty and rumpled hair, his casual appearance and this aura of relaxation he seems to emit. 

 

Nobody can blame Dean for having a hard time believing that he’s actually standing in front of the guy he has seen about a week ago in a small, smelly gym. The one he has dubbed the most gorgeous guy he has ever seen, after looking at him for less than three seconds. The one he thought he’d probably never see again- and if he did, he wouldn’t have the courage to actually approach him. 

 

And, seriously, how lucky can a guy be? Dean is actually standing right in front of this dude, in his house, and he’s about to have a conversation with him! He’s able to spend time with him! The universe must like him a little, after all.

 

Once his brain seems to switch back on, Dean jumps off the couch and immediately thrusts his hand out towards the guy, who must be the younger brother named Castiel. His hand hovers between them awkwardly for a few seconds, until he realizes that Castiel is still carrying the tray with both hands and has no way of returning his handshake. He quickly drops it again and starts blushing like crazy. 

 

Way to seem smart and attentive, Winchester. Dammit… 

 

Even though his face is probably the shade of a ripe strawberry by now and all he wants to do is hide, he can’t help but take another look at Castiel’s face before awkwardly sitting back down on the couch. Something like surprise seems to flit over his features, but it’s immediately replaced by a neutral smile. 

 

“Uhm, hi! Hi, I’m Dean Winchester. Sammy’s big brother.” He smiles and watches as the younger brother puts the tray down on the table and takes a seat next to him on the couch. 

 

When Castiel finally shifts towards Dean, it’s with a huge grin. “I’m Castiel.” Shit, that voice! “Claire’s brother, if you haven’t already figured that out,” he chuckles, and damn that sounds incredibly nice, as well.

 

Well, then… Maybe he doesn’t remember him? It’s probably a good thing, considering the unabashed way Dean had been staring at him back at he gym. Still, he can’t help but feel a weird twinge of disappointment at the fact that Castiel doesn’t remember him at all- but he tries to ignore it.

 

“Yeah, uhm… Sorry, I’m kinda nervous,” Dean mumbles, looking at the tangled hands in his lap.

 

Cas just pats his shoulder and sends him a warm smile. “I prepared some cherry tea and chocolate cookies, grab whatever you want! And if you want a different snack, you just need to tell me.”

 

“Oh, wow, thank you! I’m more than happy with cookies, though.” Dean snatches one immediately. “So, you guys are Claire’s caretakers?” 

 

“Yeah. We try to split the responsibilities. See, I own a bakery and I have crazy hours. I usually have to be over there at 4 in the morning,” Gabriel answers, starting an easy conversation and babbling away. He treats Dean as if they’ve known each other for years and Dean immediately feels a lot more comfortable.

 

Dean learns that Gabriel is twenty-six and owns a bakery (he actually baked the cookies) and has horrible hours. Castiel, who is twenty years old, is in med school and works late shifts at a Gas ‘n’ Sip. The two actually plan their days and schedule when each of them spends time with Claire, so that she’s never alone. Their father Chuck, a paranormal fiction author, spent almost all of his time travelling ever since his wife died seven years ago. The last time he actually visited them was 14 months ago, and he didn’t even stay for a whole week.

 

Claire apparently doesn’t care much about the fact that her father abandoned them, at least that’s what she tells her brothers on a daily basis. It doesn’t take Dean more than ten minutes with them to know without a doubt, that Gabriel and Castiel love Claire with all of their hearts and that they would do absolutely anything for her. They are undoubtedly good caretakers, good brothers and good people.

 

When Castiel starts talking about his studies, Dean is mesmerized by how passionate he is about absolutely everything related to medicine and biology. Dean is so focused on listening to Cas that he doesn’t even realize when Gabe leaves the room somewhere along the way. 

 

Talking to Castiel just makes him even more fascinating to Dean. He’s passionate, caring, intelligent, helpful, polite and witty. He wants to be a doctor, wants to specialize on paediatrics. He’s in med school to be able to actually help people one day. He’s… just amazing.

 

They talk about careers, about hobbies, about their siblings. They talk until Gabe enters the room and asks them to join him in the kitchen. Apparently, Dean completely missed that the kids came downstairs about an hour ago and Gabe left to cook some lunch for them. He’s been to absorbed in his conversation with Cas… Shit, he’s got it bad already.

 

When Dean gets up from the cozy leather to follow Castiel’s retreating form, he feels as if he had just been pulled out of an amazing dream. 

 

He’s being pulled out of this haze as soon as he enters the kitchen with Cas. Claire and Sammy are already seated on a big, wooden table, swaying in their chairs and giggling as Gabriel places a deliciously smelling lasagna in front of them. Dean plops down next to Sammy and glances at the clock above the door, only to realize that it’s already early afternoon. How did time fly like that? 

 

They eat and chat in the sun-flooded kitchen, and Dean realizes that he has never felt more at home in someone else’s house than he does right here, with the Novak’s. The food is excellent, and both Dean and Sam tell Gabe so several times. 

 

After lunch, the two Winchester brothers get ready to leave. When the three oldest ones start saying their goodbyes, Claire and Sam immediately leap at the chance of having a few more minutes to play, get dressed and rush outside.

 

Dean watches them from the doorstep, smiling to himself.

 

“Dean, thank you so much for agreeing to this and visiting us,” Gabriel starts.

 

“Hey, guys, thank you! Today was very nice, thanks for feeding us and suffering through our company! Sammy is probably the luckiest he’s ever been,” Dean grins.

 

“We’re seriously thankful for this, Dean,” Cas chimes in. “Claire has had a hard time making real friends, and Sam is her first, genuine friend in a very long time. We’ve… we’ve been worried. But she talks about him constantly, and she’s so much happier ever since they became friends. You raised an amazing boy, I hope you know that.”

 

Dean blushes again, but is quick to respond, “Um, thanks! Sammy really is a great kid. But, same goes for Claire. Sam is ecstatic whenever he talks about her, I think they are really good for each other.” He casts another look outside, watching as two small figures pick daisies in the front yard. 

 

“I think so, too,” they say in unison and grin. 

 

Before Dean can turn to leave, Cas slips him a small piece of paper with his and Gabe’s name, and two phone numbers. “So we’re able to plan further ‘play dates’,” he says with a smile and dorky air quotes.

 

“Awesome! Well, then. We better get going.” Dean says and turns with a wave of his hand. “Bye, guys!” 

 

He watches as Claire gives Sammy a tight hug and runs back inside to her brothers. Before the door falls shut behind them, however, Dean hears Castiel’s distinctive voice. “I’ll see you again at the next basketball game, Dean!” 

 

Uhm, what??

**Notes for the Chapter:**

> Thank you so much for still keeping up with my lazy ass.   
> I honestly appreciate every single comment!! <3
> 
> I really don't want to promise anything again, but... I have many important parts of the next chapters already mapped out. Maybe the next updates will be faster. :(
> 
> I'd love to talk to you!! Find me on [Tumblr](https://suckerfordeansfreckles.tumblr.com/)?


	6. Chapter 6

**Summary for the Chapter:**

> Dean and the Novaks plan some more meetings and trips for Sam and Claire, and Dean silently pines away.  
> Until the two kids finally bring his crush on Cas up.

**Notes for the Chapter:**

> I'm so sorry it took me so long to update this, AGAIN :( This chapter is at least a little longer than the others, though. So, maybe you can accept that as a little... idk, apology-gift?
> 
> I feel horrible... but I've been sick since Tuesday evening and I honestly struggled a lot with this chapter. But- here it is, finally!

It’s only two days after they first met, on the following Monday, that Dean decides to text the Novaks. Sammy had asked him right after coming home on Saturday if Claire could visit him and see their apartment soon. Dean had to check his schedule at the garage first, but once he was sure he could clear Wednesday and spend the afternoon at home with Sam and Claire, he starts composing a text.

 

Dean is a little ashamed to admit this, but he ends up debating for about an hour which brother to text, in order to ask if he could pick Sam and Claire up from school on Wednesday. He decides to contact Gabe, because… it would be weird texting Cas, right? He might think that Dean is… clingy or annoying? 

 

The logical part of his brain knows that Cas would totally understand that the text is about the kids… but Dean’s anxiety flares up just thinking about texting him and tells him to be extra careful, as to not accidentally reveal how he feels about Castiel. Not that there are any serious feelings. But Cas knowing that Dean thinks he’s cute would… undoubtedly make things weird.

 

When he gets an answer from Gabe, his stomach clenches just from reading it. Instead of telling him whether or not he can pick Claire up, his text says: Hello, Dean-o. Cassie’s the one responsible for her after school. I don’t think either of them have plans for Wednesday, but you better check with him

 

Well, shit. Seems like he can’t avoid texting Cas. He flops down on the couch next to Sammy, who’s absolutely mesmerized by an episode of some nature documentary about life under the sea and doesn’t even notice his brother’s predicament. When he starts typing the message and notices his stomach clenching again, it leaves him wondering why the hell he even is this nervous about texting a guy. Not like he’s a blushing virgin. What’s going on with him??

 

Hi, Cas. It’s Dean Winchester :) Just wanted to ask if I could pick Claire and Sammy up from school on Wednesday and take them back to our place. I can drive her back whenever you want her to be home

 

Sent. Done. Why would Cas even think it’s weird of him to text him? Dean’s just overthinking this whole thing.  
Hello, Dean. That’s very nice of you to offer- I can pick Claire up, though. Just send me your address and a time!

 

Once every is settled, Dean leans back and tries to focus on the documentary Sam is watching. Cas is a nice, normal guy. There honestly is no reason for Dean to be so nervous about interacting with him. He takes a deep breath and starts thinking about what to cook for the kids on Wednesday.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

Wednesday with Claire is really pleasant, and Dean, once again, has to admit to himself that the Novaks are probably his new favorite people. Sam was absolutely right about Claire, she is an amazing girl; nice, polite, adventurous, creative and very imaginative. Even though she’s already 12 years old, she builds imaginary worlds- yes, Dean may have eavesdropped a little to hear if the kids are getting along well- that amaze even him. 

 

When Cas comes to pick her up around seven, Dean opens the door and immediately knows that he’s going to need a few seconds to catch his breath. Cas, though completely soaked from the rain, looks amazing; dark hair a wet mess, damp jacket clinging to his broad shoulders, cheeks a little pink from the cold. God, there seems to be no possible situation in which Castiel would not look absolutely breath-taking.

 

Cas steps inside and they chat a little about work and school in the hallway, waiting for the kids to finish up. He tries to learn as much as possible about Castiel’s upcoming week, soaks up every word he speaks, and manages to steal a few seconds in between to admire Cas’ gorgeousness. When the two Novak siblings actually do leave, he finds he might even be as sad about it as Sam is.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

It goes on that way for the next few weeks, Dean and Cas arrange meetings and the kids are over the moon whenever they get to spend a few hours with each other. Dean tries to get a little creative with how to spend all this time with them, takes them out to the park or the zoo whenever he has the time. Cas, apparently, starts taking them to museums and art galleries. 

 

Dean was a little perplexed when Castiel first told him about that, because… two pre-teens in a museum? There’s no way that’s not going to be horrible for Cas. Having to keep them from doing something dumb, having to keep them quiet and keep them interested?? But Sam came home gushing over whatever exhibit they’ve visited (something about ancient Egypt?) and, honestly, Dean should have predicted that. Both Sammy and Claire seem to absorb knowledge of any kind, no wonder they love trips like that. Cas definitely knows what he’s doing.

 

Sammy’s weeks seem to start evolving around when he gets to see Claire. He’s absolutely in love with basketball and Bobby profusely assures Dean that he’s doing great whenever they get to talk after he drops Sam off from practice. The next game is a few days, so Dean is going to see his progress in person soon, anyways.

 

Dean can’t deny that he looks forward to seeing Castiel, as well. He lives for the few minutes he gets to spend with Cas whenever it’s time for one of them to pick their respective kid up from the other’s place. They never have a lot of time to talk, but they somehow still manage to get to know each other even better over the next three weeks. It feels nice to be somewhat included in Castiel’s weekly schedules, to be a part of his life- albeit just a small one.

 

And the more Dean learns about Cas and his life, the harder he falls for him. He can’t even contain how happy he is whenever he gets to see Cas anymore. He must be freaking obvious, staring and blushing and babbling away every time he so much as looks into bright blue eyes. 

 

He thinks about that a lot, but since nobody ever addresses the topic, he just ends up thinking he and his feelings are safe and secret. 

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

 

It’s only when the picks the kids up from school to take them back home once again that he realizes that other people might have actually caught on to his crush.

 

They have been driving for about ten minutes when they reach a red light and Sam and Claire stop talking for the first time since entering the car. So, obviously, Dean leaps at the chance to ask about Castiel.

 

“Hey, um, Claire. How’s Cas doing? I know he’s been pretty stressed lately, what with all the exams and stuff, has it gotten any better?” Dean asks as nonchalantly as possible, fingers drumming on the steering wheel.

 

She snorts a little and Dean’s head shoots up immediately, watching her through the rear-view mirror for a few seconds. When she answers, she’s grinning at Sam and her eyes twinkle mischievously. “Oh, he’s fine. He’s done with most of his exams by now and has a lot more free time. Why are you asking?”

 

“I was just wondering,” he mumbles, fixing his gaze on the road again.

 

“You ask a lot about Cas. A lot more than about Gabriel… Do you not like Gabe?” It’s Sam, this time, and Dean can actually hear how hard he’s smirking just from the tone of his voice.

 

“No! No, I like both of Claire’s brothers. Cas is just… Cas and I are closer in age, so we get along better?” It sounds more like a question than an answer, and Dean immediately knows that the two sneaky little devils won’t drop the topic now. Dammit, why is he this unconfident when it comes to Cas?

 

“Is that so?” Sam asks. 

 

“Or do you maybe have a huge crush on Cas?” Claire continues. “Because that’s what Sam and I think. You’re not very subtle with all the staring and the dreamy sighs.” 

 

“Wha- no! I don’t have a crush on you brother. And I most definitely do not sigh dreamily around him!” Dean grumbles defensively and grips the steering wheel a little tighter. Yes, maybe he does have a (rather huge) crush on Cas. But he’s also 19 years old and had a lot of crushes before, shouldn’t he be better at hiding them?? Or, at scoring a date? 

 

“Dean, you know you don’t have to deny anything. We won’t tell Cas or Gabe about this,” Sam says soothingly.

 

“And, you know, Cas is into guys. He’s also a lot more social around you than he has been around… anyone, ever. I’m pretty sure he likes you, too.” Claire speaks up again.

 

“He- he is into guys? Are you sure?” Dean feels a huge bubble of hope filling his chest, but he tries to contain just how happy this new information makes him. Shit, that was his biggest fear all along- finally telling Cas and him being offended by his feelings, or-

 

“Do you want some help with this? Claire and I could help you win Cas over,” Sam interrupts his thoughts enthusiastically. “We made a list, just like you and I did back when you helped me befriend Claire!! You could finally start wooing Cas!”

 

“Guys!” Shit, they’ve put thought into this! If two pre-teens are cooler about this than he is… Maybe they could actually help him. Claire does know Cas very well. “Okay, you know what- Tell me about that damn list.”

**Notes for the Chapter:**

> A huge thank you to everyone who's still reading this fic, I'm so sorry you have to suffer through me and my laziness :( <3
> 
> You can find me on [Tumblr](https://suckerfordeansfreckles.tumblr.com/)! I love talking to you guys :)


	7. Chapter 7

**Notes for the Chapter:**

> I am so sorry. I'm lazy and horrible! 
> 
> Buuut, here is a cute new chapter.

**STEP 1: Bond over something _(BOOKS!)_**

 

When Dean drives Claire home that day, he actually feels kind of positive about this whole thing. The kids sat him down and showed him their list; an actual, thought-out, list. With bullet points and shit. They actually meant it when they said that they had an honest-to-god plan about how Dean could woo Cas. And with how much they care about it, how could he deny their help?

 

When they arrive, Claire and Sam nag Cas about getting a few more minutes to play, and finally leave Dean and Cas in the hallway with matching grins. 

 

“Hello, Dean,” Cas says again, a smile on his face. “Do you maybe want some tea? Or a coffee? That would give the kids some more time.”

 

“Yeah, sure. A cup of coffee would be nice. I have a shift coming up,” Dean sighs. 

 

He follows Cas into the kitchen, thinking about how to best approach Claire’s first suggestion. Apparently, Cas loves talking about books, and Dean should take advantage of that.

 

“A shift at the bar, right?” Cas asks as he turns his back to Dean and starts the coffee maker. 

 

“Yeah.” Dean watches for a minute as Cas prepares their drinks, muscles on his back shifting with every move. When Cas reaches up to grab two cups from a shelf above his head, and his shirt rides up and exposes the dimples on his lower back, Dean has to clear his throat and distract himself from the view by continuing their conversation. “So, Cas. Claire told me you’re almost done with your exams and finally have more time to yourself, how are you using it?” 

 

“Oh, well, she’s right. I actually only have two more exams coming up, and I’ll be done in two weeks. I try to spend most of my time with Claire, actually.”

 

“That’s lovely,” Dean says, a soft smile spreading over his face. 

 

“And the rest of my time, I use to study. Or read,” Cas grins, turning around with a cup of coffee for Dean, and tea for himself.

 

“Yeah? What do you read?” Dean asks, trying for casual as he takes his coffee from Castiel’s hand and leans against the kitchen table. 

 

“Pretty much everything, to be honest. Do you have a favorite author?” Cas sounds excited now, and Dean finds himself thinking that this couldn’t have gone any better. 

 

They continue to talk about books and authors and favorite genres animatedly for about half an hour, and only end their conversation when Dean remembers he has to work in an hour. Cas is ecstatic when he runs upstairs to send Sammy down and grab his favorite book to lend Dean.

 

They say their goodbyes and Dean promises to bring his own favorite, _Cat‘s Cradle_ , for Cas to read next time.

 

**STEP 2: Make him his favorite food _(BURGERS!)_**

 

„Wow, it smells amazing in here.“ Cas‘ grin stretches from cheek to cheek when Dean opens the door for him.

 

“I made some burgers, the kids were about to start eating. Do you and Claire want to join us, or are you in a hurry? Claire told me you like burgers,“ Dean says, backing up towards the kitchen with a questioning look. 

 

“Honestly, I’d love to join you. Burgers make me very happy,“ Cas beams, taking his shoes off and following Dean inside.

 

“I even made some fries!”

 

**STEP 3: Surprise him with something nice**

 

“Heya, Cas,” Dean greets him with a grin, holding a cup of coffee out towards him. “I brought you some coffee, I heard your coffee maker isn’t working and you’re low on caffeine.”

 

Cas is beaming when he takes the cup from Deans hand. “You’re a life-saver, thank you so much! I’ve got an essay to finish today, I wouldn’t be able to do that without some coffee.” 

 

Before he can even process what’s going on, he has his arms full of Cas. Of deliciously smelling, beautiful, smiling Cas, hugging him tight.

 

**STEP 4: Impress him with your brain _(Bees. He’s obsessed with bees.)_**

 

“So, honey, huh?” Dean blurts, watching Cas prepare some tea.

 

“Yes, honey. It’s a great sweetener, and also very healthy,” Cas grins, sitting down next to Dean on the kitchen table.

 

“Yeah, I know! I love honey. I love bees. They are great.” He’s sure he’s blushing like crazy, but how the hell could he have been smoother about goddamn bees?

 

“They really are! Did you know that honey bees can fly at a speed-”

 

“Of 25 km per hours? Yeah, it’s crazy!” 

 

Cas smile is ridiculously big, and it makes Dean feel fuzzy and warm. That smile was definitely worth learning random facts about bees for an hour last night. 

 

Dean barely manages to suppress a proud grin. “I’ve read an interesting study just yesterday, about how bees change their brain chemistry when they change their jobs in the hive…”

 

**STEP 5: Bake something for him _(Maybe pie? Cas loves blueberries + honey)_**

 

He lets Claire hand the pie over— because this is seriously ridiculous. He spent an hour and a half baking pie for Cas last night, he is _that_ gone on the guy. And he can’t hand it over, too. He does not want to make a fool of himself, after all.

 

“Dean made some pie for us,” she grins, shoves the pie into Cas’ hands and walks into the house. “It’s blueberry. For you, actually,” she stage whispers.

 

“You— You made pie for me?” Cas looks a little confused, but happy all the same.

 

“Yeah, I know this is dumb… Sorry. Gabe’s pie is probably worlds better than this. Claire just dropped that you like blueberries, and. I felt like baking, I don’t know. Not a big deal,” he mumbles, and he can feel his cheeks burning in embarrassment. Why is he always blushing around Cas? “Also, y’know. To celebrate you acing all your exams.”

 

“God, Dean. You’re amazing!” Cas leans in and presses a kiss to his cheek. A kiss. With his lips. On Dean’s cheek! “Gabe refuses to make me blueberry pie, says he’s made too much of it in his life already,” Cas chuckles. “Seriously, thank you so much. Do you want to come in and share?”

 

**STEP 6: JUST ASK HIM OUT, DEAN. _PLEASE!_**

 

“Hello, Dean!” Cas greets him with a grin and beckons him in. “Sam and Claire are watching a movie and there are about 20 minutes left for them to watch. Would it be okay if they finish it now, or do you  
want them to watch the end the next time Sam comes over?”

 

“No, no. Let them finish, I’m not in a hurry.” 

 

“You could join me in the kitchen, I’m cooking dinner,” Cas says and turns to walk back into the kitchen, already knowing that Dean will follow.

 

Today is the day. Dean has promised Sammy and Claire that he’ll ask Cas out today. Well, maybe it wasn’t so much of a promise and more of a… plight under their blackmailing. Whatever, he has to go through with it today, or _they_ will ask Cas for him. And Dean can’t let that happen, he just can’t.

 

He’s been nervous all day, but now that he’s actually standing in this damn kitchen, watching Cas stir in a pot, a polka-dotted apron around his waist, he can actually feel his heart beating in his throat.

 

In the end, like it is with most things concerning Cas, Dean loses control and just ends up just blurting it out. And stumbles over his words, of course.

 

“So, um, Cas. I- I was wondering if, maybe, we could hit the movies this weekend?”

 

“Oh, yes, I’d love that! What movie were you thinking?” 

 

He’s smiling. He’s smiling and he said yes!! _YES!_ Dean’s feeling dizzy just looking at Cas.

 

“I mean, I could pick you up and we just see what movies they are showing? If that’s okay?” He’s blushing again, dammit. But he’s also feeling so happy, he isn’t even ashamed.

 

“That would be great! How about this Saturday?”

**Notes for the Chapter:**

> Talk to me on [Tumblr](https://suckerfordeansfreckles.tumblr.com/) ? I swear I'm nice :)


	8. Chapter 8

**Notes for the Chapter:**

> Hi again!!
> 
> I don't know why, but I was very motivated to get the next chapter done. Given the horrible upload habits I've had so far, I decided to post this as soon as it was done. Kind of as a sorry to you guys!
> 
> So, I hope you enjoy it <3

Sammy flops down on Dean’s bed face-first. “Have you decided what you’re gonna wear yet?”

 

“Do you think I’d still be walking around half-naked if I had?” Dean sighs and flops down next to his baby brother. “What do you think I should wear? Somethin’ nice? I mean, were just going to the movies, it’s not that special…”

 

“I don’t-“

 

“Should I have picked something nicer for our first date? Do you think he thinks I’m boring?” Dean asks alarmed and sits up to look at his brother, who’s still lying on his tummy. “Sammy, do you think he thinks I’m cheap?”

 

Sam sighs, long and suffering, and rolls over to grab Dean’s face in his hands. He pulls his head down a little to bring them at eye level, and squeezes his cheeks between his palms. “Dee! Relax! He said yes, didn’t he? He wants to do this, so you gotta calm down and be cool about it.” 

 

“Damn, I’m trying. I really am. Cas just makes me… go a little dumb.” He sighs, petting Sammy’s hands. “Alright, I’m just gonna wear a nice shirt and jeans. That’s half casual and half nice. Should work, right?”

 

“Yeah, Dee. It’ll work. I’m pretty sure Cas is as into you, as you are into him— don’t worry,” Sam smiles, dropping his hands back down into his lap. “Now go get dressed!”

 

“Alright, alright, boss.” He quickly jumps into some nice jeans, a grey button-down and puts on some cologne. They are interrupted by the ringing bell ring. “That’s gotta be Bobby. Go let him in, please?” 

 

Sam sprints to let Bobby in, and Dean grabs his wallet and keys and joins them in the hallway. Bobby looks incredibly tired, but he’s indulgently smiling at Sam, who’s apparently made it his goal to tell Bobby about Cas and Claire and the list and how Dean is “so hard in love, it’s really funny” in about two minutes, nonetheless. 

 

“Alright guys, I’m gonna head out. Thanks again for babysitting, Bobby,” Dean smirks as he rounds them and heads for the door.

 

“Hey, jerk, I heard that!” Sammy glares. 

 

Bobby grumbles at the swear word. “Yeah, yeah, boy. Just call if you need somethin’, and don’t come home too la-” 

 

“And good luck, Dee!! Don’t be nervous! And don’t be gross! Bye!” Sam laughs, grabbing Bobby’s arm and pulling him towards their living room.

 

“Oh shut up, squirt. See you guys later, thanks for everything.”

 

 

The drive to the Novaks’ place is absolutely horrible. Dean checks his breath twice, and his face in the rearview mirror three times. And are his pants really zipped up properly? Is there something in his teeth? Is the car clean enough for Cas?

 

He’s relieved when he actually pulls up in front of their house, because that means he only has one more chance to check his face in the mirror before he has to walk up to the door and actually face Cas. 

 

He almost trips twice on his way to the door, and he’s really close to bursting out in nervous laughter when he actually reaches it. He’s a nervous wreck, and all he wants are a few more seconds to breathe, which makes it even worse when the door flies open in front of him immediately. 

 

“Hi, Dean. We need to do this quick, we have a problem!” It’s Claire greeting him, and she looks as out of breath as she sounds. “Cas’ll be down in a minute or two, and he thinks you two are taking me and Sam to the movies! I don’t know what you said, but it was the wrong thing. You either have to tell him the truth, or conjure Sam up somehow.” 

 

“W- What?” 

 

“I’m sorry, you’ll have to make a decision. I’ll go and try to stall you some time,” she says and closes the door behind her without another word.

 

And, fuck. What? Did he really already fuck this up? Did he not even manage to ask Cas out? He’s such a loser...

 

Fuck, he has to call Bobby!

 

He sprints back to the car to grab his phone and dials Bobby. It rings, and rings, and wow, Dean is having a panic attack. A deep breath, it rings again, another breath, and finally: “Yeah, Dean? Everything alright?” 

 

“Bobby, listen. I’m so sorry, but I need your help. I somehow fucked this up and Cas thinks Sam’ll watch the movie with us. Can you maybe drop Sammy off at the cinema in 15 minutes? Act like you had something important to do, or something? Man, I’m so sorry. This is not a date, apparently.”

 

“Hey, calm down! I’ll drop Sam off, don’t worry.”

 

“Thank you so much,” he breathes.

 

“I’m sorry you didn’t get your date, boy,” he mumbles. “See you in 15.” Bobby hangs up, and Dean is left standing on the sidewalk, still struggling to breathe regularly.

 

“Yeah, I’m sorry, too...” He fucked up. He can’t even get a date, apparently. He didn’t explicitly call it a date, that’s true— but he’s pretty sure that he was clear about wanting to go out with Cas. Him and Cas, alone. Not with the kids. Wasn’t he? 

 

Maybe he was clear about it, but Cas just didn’t want to go on a date with him? He could have easily made this about the kids to dodge Dean’s advances. Is this his way of telling Dean that he isn’t interested? Shit, and now he’s overthinking everything!

 

He gets about three deep breaths in before the door opens again and Claire walks out, followed by her brother. Cas looks… Cas looks ridiculously beautiful, soft smile and crazy hair, in black jeans and a blue henley. He waves enthusiastically as soon as he sees Dean, his smile widens impossibly, and suddenly Dean is a lot less worried. 

 

“Hello, Dean!” 

 

“Hey, Cas.” It comes out a little breathless, but not as bad as Dean thought it might. 

 

Claire looks at him with a very obvious question in her eyes. Are you gonna man up and tell Cas that this was supposed to be a date, or not?

 

“So— So, we’ll meet Sam at the cinema.” How ridiculous is it that he can’t even look into Claire’s eyes? She’s just a kid, dammit. “Uncle Bobby is gonna drop him off, they had… they were spending the day together. Alright, jump in the car, guys.”

 

 

The time it takes for them to get to the cinema is filled with awkwardness. About 5 minutes in, Claire starts talking about a film that just came out and that she would like to see. She doesn’t stop talking until they are actually parked in front of the cinema, and Dean couldn’t be more thankful because he couldn’t have dealt with more awkward silence. Dean glances through the rearview mirror a few times while driving, trying to catch Cas’ eyes while avoiding Claire’s annoyed glare. Cas looks a little wary, as if he realizes that something is off.

 

They meet Sam in front of the cinema, and he’s frowning like crazy, grabbing Dean’s biceps as soon as he’s in arm’s reach. “Dee, what the hell,” he hisses through clenched teeth. 

 

“I fucked it up, somehow. Now shut up.” It’s an angry whisper, accompanied by a careful shove with his elbow. Louder, he says: “We haven’t been to the cinema in ages, Sammy. Isn’t this great?”

 

“Yeah, unbelievable.” He sends another glare towards Dean before addressing everyone in their tiny, odd group. “So, what movie are we gonna watch?”

 

They decide— or rather, Claire decides— that they are going to watch Love, Simon. Claire and Sam also decide that they need seats away from Cas and Dean, at least three rows between them, because everything else would be “super embarrassing”. 

 

 

That’s how Dean finds himself in a row of seats in the front of the cinema next to Cas, popcorn in his lap. The row is completely empty, except for them, because nobody in their right mind wants to sit that fucking close to the screen, obviously.

 

The commercials are finally over and the movie starts, and Dean is glad he doesn’t have to try to strike up a conversation with Cas anymore. He shifts back and forth in his seat, unable to get comfortable. When his knee bumps against Cas’, he almost jumps out of the dumb faux leather seat because this whole thing is so awkward. 

 

They watch the movie for what feels like an eternity, but probably weren’t more than 20 minutes, and Dean has to actually squeeze his fingers into his thighs to keep from turning to his side and just watch Cas instead.

 

There’s a quiet “Wait!” from Cas’ direction, and Dean finally can’t fight turning towards him anymore. His face looks weirdly angelic in the soft blue light of the screen, but there’s a baffled expression on it.

 

“Wait, something is up. Claire has been very annoyed about this, Sam wasn’t even…” He turns towards Dean, now. “Dean. Was this supposed to be a date?”

 

“Wha— I mean, a date? It’s, y’know... yeah. Yeah, it should have been,” he sighs. 

 

“Oh, Dean. I’m such an idiot…”

 

“No, don’t worry. It’s alright. I get it if you don’t want-”

 

“Stop right there, please. I would love to go on an actual date with you. Without the kids,” he chuckles and brings his hand up to cup Dean’s burning hot cheek. “I would also love to kiss you now. ‘Cause I’ve been thinking about that for weeks,” he trails off, looking at Dean questioningly. 

 

“Yeah, you should do that,” he breathes, and leans towards him, over the stupid armrest that separates them, and right into his Cas’ space.

 

Cas leans in, too, and the first press of lips already makes Dean addicted. They deepen the kiss when Dean opens his mouth a little, and he almost loses his mind when Cas slips his tongue into his mouth. His lips are so much softer than they look, and he tastes a little of popcorn, but mostly just of Cas— and it’s everything Dean ever dreamt of. 

 

After a while, Cas breaks the kiss and breathlessly asks: “Is it a total asshole move to suggest to move this back to your car?”

 

“Fuck no, let’s get out of here!”

 

Dean’s a little sorry to miss the rest of the movie, because what he’s seen of it so far was really cool. But he’s got Cas’ hand in his, and they are on their way to his car to make out, and Dean hasn’t been this giddy in years.

**Notes for the Chapter:**

> The story obviously finally takes a term into a little steamier territory, so... I hope you don't mind?
> 
> You can find me on [Tumblr](https://suckerfordeansfreckles.tumblr.com/). I'd love to talk to you over there!


	9. Chapter 9

**Notes for the Chapter:**

> Hi, hello!!
> 
> It's getting a little steamier in this chapter... so, if you don't want to read anything like that, maybe skip this chapter.

They only make it two steps out of the cinema before Cas is already pressing Dean back against the door, moving in to kiss him. His fingers are still woven between Dean’s as he presses himself to his chest, soft, chapped lips capturing Dean’s plush ones in their second kiss. 

 

“I didn’t think I’d actually get to do this,” Dean breathes against Cas’ mouth when they part. 

 

“Neither did I. But, fuck, it’s better than I ever thought it’d be,” Cas chuckles. 

 

It’s getting dark around them, but they are standing in the harsh light of the neon sign above the cinema entrance, and there’s already a lady angrily staring at them.

 

“Alright, c’mon! Let’s get to the damn car already,” Dean laughs, starting to pull Cas with him.

 

When they finally reach the car, Dean fumbles with the keys for way too long, hands trembling with nerves. He never even let himself hope to get this far with Cas, and he has no idea where to go from here. Is he supposed to climb into the back seat, or is that too suggestive? The front seat, then? Is Cas planning on actually making out in his car? Or does he just want to talk? Or does he maybe want even more than just a few kisses? God knows Dean wants more.

 

He’s saved from his mental rambling when Cas takes the key from his hands, unlocks the car, and starts climbing into the back of the Impala. “You comin’, handsome?” He grins at Dean, petting the leather seat besides him. 

 

It’s all Dean can do to scramble into the car and join Cas, grinning like crazy. After closing the door behind himself, he sits down on the leather seat of his car and turns towards him with a shy smile. “So, um— what are we doing here, Cas?”

 

“I was hoping to get some more kisses?”

 

“Yeah, but… Y’know, is this a one time thing?” 

 

“What? No! I mean, if you want it to be... But I thought it was quite obvious that I like you. And I want to go on dates with you, build a serious relationship, be your boyfriend.” Cas blushes and, dear lord, he looks gorgeous. Dean can’t help but let his fingers brush over pink cheeks and dark stubble.

 

“No, I really, really don’t want this to be a one-time thing. I’m all for dates, and serious, and boyfriend.” He smirks, leaning closer and placing a tender kiss on Cas’ lips. “I’m also very much for making out.” 

 

“Then everything’s settled,” Cas grins, and pulls Dean up and on his lap. Dean straddles him, one leg on the leather on either side of Cas’ legs, ass planted firmly on his thighs.

 

Cas grabs his neck with both hands and gently pulls him down and into a heated kiss. He’s all heat and desire right away, kissing and licking, until Dean feels dizzy with need. His hands wander over Dean’s thighs, up to his hips, and back down again to palm his ass through his jeans. Dean gets his fingers back into Cas’ soft, wild hair, and when Cas moans into their kiss, he can’t help but pull a little on his dark locks.

 

When Dean scoots a little closer to bring their chests together, he inadvertently brings their groins together, too. All the air in his lungs rushes out of him at the delicious friction this creates, but it’s when he realizes how goddamn hard Cas is against him, that he actually lets out a pathetic whimper. 

 

“Fuck,” he breathes, grinding down against Cas’ clothed dick again, not even ashamed about the noises he’s making.

 

“Shit, Dean. You sound so pretty,” Cas says, voice raw with want. 

 

“Cas,” His breath hitches a little as he moves down against him again, pressing his face into the crook of his neck, “Cas, are we really doing this? In my car? I mean, fuck, we haven’t even been on an actual date yet.”

 

“I feel like I know you very well already, and I don’t think a date would change much between us. But if you’re not comfortable with this, or want to wait, that’s absolutely okay.” Cas says, and lessens his grip on Dean’s ass immediately. But judging by the way his hips hitch upwards slightly on their own account, and the ridiculously huge bulge in his jeans, it’s obvious he’d very much like to continue this.

 

Dean lifts his head from Cas’ shoulder and takes a quick look at his watch. “We have twenty minutes ‘til the film ends. We should be in there when that happens, I really don’t want to have to explain this to Sammy or Claire,” he says. 

 

“So, do you want to…?” Cas trails off with a hopeful look, bringing one palm back up to cup Dean’s cheek.

 

“Fuck yes I want. But I’m also gonna take you out on a date tomorrow,” Dean says cheekily and leans in to bring their foreheads together.

 

“Tomorrow is Sunday, Dean. Where exactly do you want to take me?” 

 

“Um. You’ll just have to find out tomorrow! If that’s okay?” He’s back to shy and unsure, and he hates how easily Cas makes him flustered.

 

“That’s more than okay,” Cas says and moves to press another kiss to Dean’s lips. “Now, if you don’t mind, I’d love to spend the rest of our time in here kissing you.”

 

Cas dives back in again, and Dean is instantly sucked back into the crazy, raging desire he felt before. How is Cas making him feel like this with nothing more than a kiss? He feels like he’d probably black out if Cas were to actually touch him.

 

He’s grinding back down against him just seconds later, moaning again at how hard Cas is. They haven’t been doing anything but kissing and grinding against each other, but he seems to be just as desperate as Dean feels. And he can’t help but be proud about it, about how Cas is groaning and writhing beneath him. 

 

Dean grinds down to meet Cas’ next thrust and he loses his breath once again. 

 

“Fuck, Cas. If we keep this up, I might actually come into my pants like a virgin,” he says, out of breath. He feels sweat bead on his forehead as he keeps their rhythm as steady as possible. It’s not a very comfortable way to get off, what with his dick being trapped in his jeans and the rough fabric of his boxers chafing him with every thrust. But just being with Cas makes it all tolerable. More than tolerable, actually.

 

“I’m just as close, Dean,” he says. They give up on trying to actually kiss, both just gasping for breath against each others’ lips. Cas slips his hand down the back of Dean’s jeans and boxers, then, and when he murmurs “Come for me?” and brushes his fingers over Dean’s hole, Dean can’t hold back anymore. He comes in his pants, hard, and throws his head back to moan Cas’ name.

 

“Fuck,” Cas breathes and presses a kiss to Dean’s neck. He loses his rhythm now, pushing up against Dean erratically before he lets out one last, loud groan, and falls back into the seat.

 

“Shit, Cas. That was incredible.” Dean smiles down at him. “Just hate how sticky my boxers are already.”

 

“I agree, with both statements,” Cas chuckles. “Dean, you are amazing. I can’t wait for tomorrow.”

 

Dean blushes again, but when he looks down at his watch to check the time, his embarrassment is instantly replaced by panic. “Fuck, we’re late! The film ended 5 minutes ago, Cas! Shit.”

 

They scramble out of the car, try to get themselves to look presentable again, and run back into the cinema hand in hand, smiling like idiots. Sam and Claire are already waiting for them in front of the cinema hall, sharing a meaningful grin when they see their intertwined hands.


	10. Chapter 10

Getting dressed for their first actual date isn’t nearly as stressful as it was the last time. Dean’s a little sad that his baby brother is at Bobby’s and can’t consult him on his choices, but Sam would probably only make him nervous, so he supposes it’s good just how it is. He picks a pair of jeans that nicely hug his ass, a simple t-shirt, a red flannel, and is ready to go. Well, after meticulously preparing everything else for their date.

 

He texted Cas this morning that he’d by at his place around 5 p.m., but didn’t give him any further instructions other than “this isn’t gonna be anything fancy, so dress casual”.

 

When Dean picks Cas up, he‘s greeted with a soft smile and is immediately overwhelmed with the warmth that blooms in his heart when he realizes that this gentle smile is just for him.

 

They drive in comfortable silence that is only broken when Dean steers the car off the street and onto a small country road that is framed by trees.

 

“Are you taking me deep into the woods to murder me? How romantic,“ Cas turns towards him and sends him a cheeky grin.

 

“You’ll have to wait and see,” Dean snorts, focussing on the bumpy road in front of them. It’s still sunny outside, but the trees cast long shadows over the road.

 

When they finally come to a halt, it’s next to a small clearing. While Dean grabs some things from the trunk of his car, Cas already steps into the clearing. “You like it?”

 

“This is beautiful, Dean,” Cas breathes, spinning around and taking in soft sunlight, colourful flowers and the chirping of birds perched in the crowns of the trees around them. 

 

“I’m glad! I made some food,” Dean says, smiling up at Cas while he spreads a blanket on the grass. There’s a bag behind him, filled to the brink with tupperware boxes, bottles and glasses. “Come on, take a seat.”

 

It turns out Dean brought way too much food; bread and sandwiches, jelly, cheese, cut vegetables and fruit, some cookies and even another blueberry pie for Cas, which he earns an enthusiastic kiss for. They end up eating until their stomachs hurt, feeding each other in between giggle-fits. 

 

When they start putting the food away afterwards, the sky starts to darken and Dean thinks he couldn’t have planned this whole evening better. He gets up to carry the bag to the car and Cas moves to follow him and starts to say, “That was a beautiful evening, Dean, and-”

 

“Wait, wait, wait! We’re not done,” he smirks, turning back to Cas with his arms full of blankets and pillows. “This is gonna be the most cliché date you’ve ever been on, so we’re gonna do some stargazing. I’m not even ashamed to admit that I read like ten “What to do on the perfect date with your loved one”-type of articles before planning this, I’m that gone on you.”

 

He blushes a little when he says this, but it’s all forgotten when Cas tackles him to the ground and kisses him like he’s starving, not caring about the blankets and pillows wedged between them. He kisses him like he’s been holding back for hours — and, who knows, maybe he has been. Dean sure knows he has.

 

“You’re perfect, I don’t think I deserve you,” Cas smiles against his mouth and dips back in for another taste of Dean.

 

“Stop it and let me put down the pillows, you sap. It’ll get cold soon, and I can’t have you catch a cold because I can’t take care of you properly.”

 

They settle in between the pillows, covered by too many blankets, and just hold onto each other. Cas starts showing Dean the constellations he can spot, and Dean tells Cas about the old Greek myths he’s read about them when he was younger. 

 

After a while, Cas turns towards him, one hand resting firmly on Dean’s chest. “What now? After this date?”

 

“I’m ready. I’m ready to tell everyone, though I think Sammy and Claire already know. I’m ready to make this official. I’m falling for you, and I don’t want to have to hold back,” Dean says, and he doesn’t even blush this time. This is serious, he is serious about Cas and his feelings for him.

 

“Me too, Dean,” Cas breathes, and moves to straddle Dean. He leans down for a soft kiss and grins. “We’re going to do this.”

 

“Yes, we so are.”

**Notes for the Chapter:**

> So. That's it! 
> 
> I just want to thank everyone who stuck around and read this mess, and I'm sorry the ending is this hazy. But I feel like this fic was about their journey towards a relationship, and we're at the end of this journey now. I sincerely hope you enjoyed it! I'd love to get some feedback <3
> 
> I'd also love to talk to you over on [Tumblr](https://suckerfordeansfreckles.tumblr.com/)!


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